1-Phenyl-4-nitro-5-methyl-pyrazol | 90946-25-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-Phenyl-4-nitro-5-methyl-pyrazol
• 英文别名: 5-methyl-4-nitro-1-phenyl-1H-pyrazole；5-Methyl-4-nitro-1-phenyl-1H-pyrazol；5-Methyl-4-nitro-1-phenylpyrazole
• CAS: 90946-25-1
• 化学式: C₁₀H₉N₃O₂
• 分子量: 203.2
• InChiKey: IDMMHVARGCDBQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Phenyl-4-nitro-5-methyl-pyrazol 在 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 乙酸乙酯 为溶剂， 以100 %的产率得到5-甲基-1-苯基吡唑-4-胺
  参考文献：
  名称：

  与吡唑基重氮盐的高度非对映选择性 Heck-Matsuda 反应

  摘要：

  Heck-Matsuda (HM) 反应是一种强大的合成方法，适合在温和条件下形成 C-C 键。我们证明了吡唑基重氮盐是该协议中的合适试剂，使我们能够提供高度取代的环戊烯醇和环戊烯胺，具有出色的非对映选择性和对映选择性控制。

  DOI：

  10.1039/d3nj01724a
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 、 亚膦酸 作用下， 生成 1-Phenyl-4-nitro-5-methyl-pyrazol
  参考文献：
  名称：

  667.与氨基吡唑的skraup反应

  摘要：

  DOI：

  10.1039/jr9580003259

文献信息

• Reactions of pyrazoles and pyrazolium salts with complex metal hydrides and organometallic reagents. Synthesis of pyrazolines and pyrazolidines
  作者：Purificación Cuadrado、Ana M. González-Nogal、Senén Martínez

  DOI：10.1016/s0040-4020(97)00514-0

  日期：1997.6

  2-Pyrazolin-4-oximes have been synthesized by reaction of 4-nitroso- and 4-nitropyrazoles with complex metal hydrides and organometallic reagents. Furthermore, 4-nitropyrazolium tetrafluoroborates are reactive substrates towards organolithium and Grignard compounds leading to new and highly substituted 4-nitro-3-pyrazolines and 4-nitropyrazolidines. The formation of 3-pyrazolines is regioselective

  2-吡唑啉-4-肟是通过4-亚硝基和4-硝基吡唑与复杂的金属氢化物和有机金属试剂的反应合成的。此外，4-硝基吡唑鎓四氟硼酸盐是有机锂和格氏试剂的反应性底物，从而导致新的和高度取代的4-硝基-3-吡唑啉和4-硝基吡唑烷。3-吡唑啉的形成是区域选择性的，并且当可能存在非对映异构体吡唑烷时，仅获得最稳定的3,4-反式和/或4,5-反式异构体。
• Pharmaceutically useful pyrazolo[4,3-b]pyridines
  申请人：Beecham Group p.l.c.

  公开号：US04833136A1

  公开（公告）日：1989-05-23

  A compound of the formula (I) or a salt or solvate thereof: ##STR1## in which: R.sub.0 is hydrogen or C.sub.1-6 alkyl; or together with R.sub.3 is C.sub.4-6 polymethylene; R.sub.1 and R.sub.2 are both hydrogen; or R.sub.1 is hydrogen, C.sub.1-6 alkyl; and R.sub.2 is CN; CR.sub.5 R.sub.6 Y where R.sub.5 and R.sub.6 are independently selected from hydrogen and C.sub.1-4 alkyl and Y is selected from hydrogen, OR.sub.7 or SR.sub.7 where R.sub.7 is hydrogen, C.sub.1-4 alkyl or C.sub.2-4 alkanoyl, and NR.sub.8 R.sub.9 where R.sub.8 and R.sub.9 are independently hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl or C.sub.2-4 alkanoyl or together are C.sub.4-6 polymethylene; or COR.sub.10 where R.sub.10 is OH or C.sub.1-4 alkyl, or COR.sub.10 is a pharmaceutically acceptable ester or amide, or R.sub.2 is hydrogen, C.sub.1-6 alkyl, or phenyl optionally substituted by halogen, CF.sub.3, C.sub.1-4 alkoxy or C.sub.1-4 alkyl, and R.sub.1 is CN, CR.sub.5 R.sub.6 Y or COR.sub.10 as defined for R.sub.2 above; or R.sub.1 and R.sub.2 together form C.sub.3 -C.sub.6 polymethylene optionally substituted by C.sub.1 -C.sub.4 alkyl; R.sub.3 is hydrogen; or C.sub.1-10 alkyl or C.sub.3-10 cycloalkyl, either optionally substituted by hydroxy, C.sub.1-4 alkoxy, thiol, C.sub.1-4 alkylthio or NR.sub.11 R.sub.12 wherein R.sub.11 and R.sub.12 are independently hydrogen, C.sub.1-6 alkyl or C.sub.2-7 alkanoyl or together are C.sub.3-6 polymethylene; C.sub.2-10 alkenyl; or phenyl optionally substituted by one or two of halogen, CF.sub.3, C.sub.1-4 alkoxy, C.sub.1-4 alkyl, hydroxy, nitro, cyano, C.sub.2-10 acyloxy, NR.sub.13 R.sub.14 wherein R.sub.13 and R.sub.14 are independently selected from hydrogen, C.sub.1-6 alkyl, or C.sub.2-7 alkanoyl; or COR.sub.15 wherein R.sub.15 is hydroxy, C.sub.1-6 alkoxy or NR.sub.16 R.sub.17 wherein R.sub.16 and R.sub.17 are independently selected from hydrogen or C.sub.1-6 alkyl; or R.sub.3 is a mono- or fused bi-cyclic heteroaryl group having up to ten atoms in the aromatic ring(s), not more than two of which are selected from nitrogen, oxygen or sulphur, other than those containing basic nitrogen, optionally substituted by one or two substituents selected from halogen, CF.sub.3, C.sub.1-4 alkoxy, C.sub.1-4 alkyl, hydroxy, nitro, cyano, C.sub.2-10 acyloxy, NR.sub.23 R.sub.24 wherein R.sub.23 and R.sub.24 are independently selected from hydrogen, C.sub.1-6 alkyl, C.sub.2-7 alkanoyl or C.sub.1-6 alkylsulphonyl; or COR.sub.25 wherein R.sub.25 is hydroxy, C.sub.1-6 alkoxy or NR.sub.26 R.sub.27 wherein R.sub.26 and R.sub.27 are independently selected from hydrogen or C.sub.1-6 alkyl; R.sub.4 is hydrogen, or C.sub.1-4 alkyl, phenyl or benzyl, each of which is optionally substituted in the phenyl ring by one or two of halogen, CF.sub.3, C.sub.1-4 alkoxy or C.sub.1-4 alkyl and is attached at nitrogen atom 1 or 2; and R.sub.x is C.sub.1-6 alkyl, halogen, nitro, NR.sub.18 R.sub.19 where R.sub.18 and R.sub.19 are independently hydrogen, C.sub.1-6 alkyl or C.sub.2-7 alkanoyl, nitrile, COOH, CONH.sub.2 ; phenyl or benzyl optionally substituted by one or two of halogen, nitro, C.sub.1-6 alkoxy, hydroxy, C.sub.2-7 alkanoyloxy, NR.sub.18 R.sub.19, C.sub.1-6 alkyl, CF.sub.3, CN; thienyl, furyl or pyrryl optinoally N-substituted by C.sub.1-6 alkyl, with the proviso that R.sub.0 and R.sub.3 are not both hydrogen when R.sub.1 is hydrogen and R.sub.2 and R.sub.x are methyl, is useful for treating inflammatory or allergic conditions.

  化合物的公式（I）或其盐或溶剂化物：## STR1 ##其中：R.sub.0是氢或C.sub.1-6烷基；或与R.sub.3一起是C.sub.4-6聚亚甲基；R.sub.1和R.sub.2都是氢；或R.sub.1是氢，C.sub.1-6烷基；R.sub.2是CN；CR.sub.5R.sub.6Y，其中R.sub.5和R.sub.6独立选择自氢和C.sub.1-4烷基，Y选择自氢，OR.sub.7或SR.sub.7，其中R.sub.7是氢，C.sub.1-4烷基或C.sub.2-4烷酰基，以及NR.sub.8R.sub.9，其中R.sub.8和R.sub.9独立选择自氢，C.sub.1-4烷基，C.sub.2-4烯基或C.sub.2-4烷酰基，或一起是C.sub.4-6聚亚甲基；或COR.sub.10，其中R.sub.10是OH或C.sub.1-4烷基，或COR.sub.10是药学上可接受的酯或酰胺，或R.sub.2是氢，C.sub.1-6烷基或苯，可选择地被卤素，CF.sub.3，C.sub.1-4烷氧基或C.sub.1-4烷基置换，而R.sub.1是CN，CR.sub.5R.sub.6Y或COR.sub.10，如上所定义的R.sub.2；或R.sub.1和R.sub.2一起形成C.sub.3-C.sub.6聚亚甲基，可选择地被C.sub.1-C.sub.4烷基置换；R.sub.3是氢；或C.sub.1-10烷基或C.sub.3-10环烷基，任选地被羟基，C.sub.1-4烷氧基，硫醇，C.sub.1-4烷基硫醇或NR.sub.11R.sub.12取代，其中R.sub.11和R.sub.12独立选择自氢，C.sub.1-6烷基或C.sub.2-7烷酰基，或一起是C.sub.3-6聚亚甲基；C.sub.2-10烯基；或苯，可选择地被卤素，CF.sub.3，C.sub.1-4烷氧基，C.sub.1-4烷基，羟基，硝基，氰基，C.sub.2-10酰氧基，NR.sub.13R.sub.14，其中R.sub.13和R.sub.14独立选择自氢，C.sub.1-6烷基或C.sub.2-7烷酰基；或COR.sub.15，其中R.sub.15是羟基，C.sub.1-6烷氧基或NR.sub.16R.sub.17，其中R.sub.16和R.sub.17独立选择自氢或C.sub.1-6烷基；或R.sub.3是具有芳香环中最多十个原子的单环或融合双环杂环基团，其中不超过两个选择自氮，氧或硫，除了含有碱性氮的基团，可选择地被一或两个取代基取代，所述取代基选择自卤素，CF.sub.3，C.sub.1-4烷氧基，C.sub.1-4烷基，羟基，硝基，氰基，C.sub.2-10酰氧基，NR.sub.23R.sub.24，其中R.sub.23和R.sub.24独立选择自氢，C.sub.1-6烷基，C.sub.2-7烷酰基或C.sub.1-6烷基磺酰基；或COR.sub.25，其中R.sub.25是羟基，C.sub.1-6烷氧基或NR.sub.26R.sub.27，其中R.sub.26和R.sub.27独立选择自氢或C.sub.1-6烷基；R.sub.4是氢，或C.sub.1-4烷基，苯基或苄基，其中每个在苯环中选择自卤素，CF.sub.3，C.sub.1-4烷氧基或C.sub.1-4烷基并附加在氮原子1或2处；而R.sub.x是C.sub.1-6烷基，卤素，硝基，NR.sub.18R.sub.19，其中R.sub.18和R.sub.19独立选择自氢，C.sub.1-6烷基或C.sub.2-7烷酰基，腈，COOH，CONH.sub.2；苯或苄，可选择地被一或两个卤素，硝基，C.sub.1-6烷氧基，羟基，C.sub.2-7烷酰氧基，NR.sub.18R.sub.19，C.sub.1-6烷基，CF.sub.3，CN取代；噻吩基，呋喃基或吡咯基，可选地N-取代C.sub.1-6烷基，但R.sub.1为氢且R.sub.2和R.sub.x为甲基时，R.sub.0和R.sub.3不能同时为氢，该化合物对于治疗炎症或过敏症状是有用的。